Three routes to indole alkaloids of the reserpine related alloyohimbine series will be investigated. They are espcially designed to provide entry into the cis hydroisoquinoline systems characteristic of the yohimbe alkaloids of the reserpine type. The three routes are: 1. Photochemically and ionically induced ring D-formation. 2. Stereochemical control via rigid lactone systems. 3. Ynamine control of stereochemistry.